Create a Hanging Bucket Effect (Handle Hooked on Rod)
I think your problem is the relative size of your wire and bucket meaning the physics has to be calculated very precisely.  I tried to set this up and had similar problems initially, and the the following steps fixed it for me:


Make sure the Centre of all of your objects is set to be near your geometry. (Object > transform > Origin to Geometry)
In Scene settings increase the 'Steps per second' (I went to 240FPS) (Scene> Rigid Body > Steps Per.
Make sure the 'Sensitivity' on the wire and the bucket are set to zero (or very close to) other wise the 'hole' in the bucket is effectively closed by the buffer this creates. (I think this is likely your problem, your objects are effectively starting 'inside' each other, and collisions are not detected if they start overlapping.


Set the Bucket and the Wire Like the below picture, and the thing it's hanging from exactly the same except untick 'Dynamic':



I get this: